HCID 20250618, compound → HCID 20250623, compound

HRID 1284855Notes

Reaction equation

HRID 1284855 reaction equation
[N:1]([CH2:4][C:5]1[CH:18]=[CH:17][C:16]2[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:19])[C:7]=2[CH:6]=1)=[N+]=[N-].[H][H]>CN(C)C=O>[NH2:1][CH2:4][C:5]1[CH:18]=[CH:17][C:16]2[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:19])[C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 20250618HCID 20250618, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20250623HCID 20250623, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

5 g of 2-azidomethylthioxanthone are dissolved in 50 ml of N,N-dimethylformamide, and 0.5 g of Pd-on-charcoal is added, in an autoclave. Hydrogen is then passed in. The reaction is monitored by means of IR spectroscopy. It has ended when the band at 2,100 cm-1 has disappeared. The reaction mixture is diluted with N,N-dimethylformamide, heated to 60° C. and filtered, the filtrate is cooled and water is added. The crystals which have precipitated are separated off by filtration and dried. 4.3 g (95.3% of theory) of 2-aminomethylthioxanthone are obtained. Melting point: 134°-136° C.

Workup

  1. filtrationfiltered
  2. temperaturethe filtrate is cooled
  3. additionwater is added
  4. customThe crystals which have precipitated
  5. customare separated off by filtration
  6. customdried

Sources & evidence

ORD record
ord-177977e591e34ce6913b6ade0685893f
Source dataset
uspto-grants-1986_01
Patent number
US04564578

Reaction notes

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